Duroquinone

Duroquinone
Structural formula of duroquinone
Ball-and-stick model of the duroquinone molecule
Names
Preferred IUPAC name
2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-dione
Other names
2,3,5,6-Tetramethyl-1,4-benzoquinone
Tetramethyl-p-benzoquinone
Identifiers
3D model (JSmol)
1909128
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.646 Edit this at Wikidata
EC Number
  • 208-409-8
279610
UNII
  • InChI=1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3 checkY
    Key: WAMKWBHYPYBEJY-UHFFFAOYSA-N checkY
  • InChI=1/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3
    Key: WAMKWBHYPYBEJY-UHFFFAOYAK
  • CC1=C(C(=O)C(=C(C1=O)C)C)C
Properties
C10H12O2
Molar mass 164.20408 g/mol
Melting point 109 to 114 °C (228 to 237 °F; 382 to 387 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Duroquinone is an organic oxidant (C6(CH3)4O2). It is related to 1,4-benzoquinone by replacement of four H centres with methyl (Me) groups. The C10O2 core of this molecule is planar with two pairs of C=O and C=C bonds.[1]

The compound is produced via nitration of durene (1,2,4,5-tetramethylbenzene) followed reduction to the diamine and then oxidation.[2]

A derived organoiron compound (η2,η2-C6(CH3)4O2)Fe(CO)3 is obtained by the carbonylation of 2-butyne in the presence of iron pentacarbonyl.[3]

The molecule has been mentioned in the popular press as a component of a "nano brain".[4]

Duroquinone was observed in a degradation products generated from pyrolysis of α-Tocopheryl acetate.[5]

References

  1. ^ J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.doi:10.1021/ja066471o
  2. ^ Lee Irvin Smith. (1943). "Duronquinone". Organic Syntheses; Collected Volumes, vol. 2, p. 254.
  3. ^ H. W. Sternberg, R. Markby and I. Wender, "A Quinone Iron Tricarbonyl Complex and its Significance in Organic Synthesis", Journal of the American Chemical Society 1958 volume 80, pp. 1009-1010. doi:10.1021/ja01537a075
  4. ^ *Fildes, Jonathan (2008-03-11). "Chemical brain controls nanobots". British Broadcasting Corporation. Retrieved 2008-03-11.
  5. ^ Wu, Dan; O’Shea, Donal F. (2020-03-24). "Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate". Proceedings of the National Academy of Sciences. 117 (12): 6349–6355. doi:10.1073/pnas.1920925117. ISSN 0027-8424. PMC 7104367. PMID 32156732.


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